This post may contain affiliate links. Please read our disclosure policy.
Our homemade pineapple upside down cake is a family favorite with a secret ingredient that takes this classic to a whole new level!
A Slice of Nostalgia!
Grandma has been making pineapple upside down cake for decades. It’s a family FAVORITE dessert that happens to be grandpa’s favorite!
This classic recipe has been slightly adapted over the years and now includes our favorite “secret” ingredient: almond extract. We know not everyone loves this extract (you can use vanilla extract instead), but no matter what you use the result is a simple buttery cake turned moist, gooey and upside down with caramelized pineapple slices on top. PURE HEAVEN!
Not only does it prep in minutes (10 to be exact) and has simple ingredients and steps, but it looks AMAZING (and tastes amazing)! It truly is a show-stopper that definitely turns heads at every function.
This homemade pineapple upside-down cake recipe is perfect all year long, but is an especially good summertime dessert along with our cupcake version!
WHY WE LOVE IT:
- That signature flavor. The pineapple juices and sugary layer ooze into the cake making it gooey and delicious!
- 10-minute prep! With a quick prep, this moist cake is showstopper that is quite simple!
- For sharing. This is an incredible summer treat perfect for barbecues, parties, and holiday get-togethers. It’s one we love to share!
Ingredients
PREP TIME: 10 minutes COOK TIME: 35 minutes
- 1 cup unsalted butter, divided – or use salted butter
- 1½ cups packed light brown sugar divided
- 1 (20-ounce) can pineapple rings in juice – Measure out ½ cup of juice and drain the excess liquid. Leave the canned pineapple pieces in a colander to finish draining or pat dry with a paper towel (fresh pineapple can be used – just peel and cut accordingly; you will still also need pineapple juice)
- 10-12 maraschino cherries
- 2 cups all-purpose flour – see How to Measure Flour
- 2 teaspoons baking powder
- 1 teaspoon salt – Reduce if using salted butter.
- ½ cup granulated sugar
- 2 large eggs- room temperature
- ½ cup milk – We use 2% but whole milk or 1% work also.
- 1 teaspoon almond extract (optional) – or teaspoon vanilla extract
- optional nuts – Sprinkle chopped walnuts or pecans in the bottom of the baking dish.
how to make Homemade pineapple upside down cake
- PREP. Preheat the oven to 350°F. Grease a 9×13-inch baking dish.
- SAUCE. Melt ½ cup butter in a medium pot over medium heat. Set remaining ½ cup butter aside to soften. Stir 1 cup brown sugar into butter in the pot and bring to a boil, stirring frequently. Continue boiling for 1 minute, then pour the melted butter mixture into the prepared pan.
- ADD FRUIT. Drain can of pineapple slices, reserving ½ cup of the juice, and place whole rings into the bottom of the cake pan. Trim the rings as needed to cover the bottom. Place a cherry in the center of each pineapple slice. Set aside.
- BATTER. In a medium bowl, whisk 2 cups of all-purpose flour, 2 teaspoons of baking powder, and 1 teaspoon of salt. Set aside.
- In a large bowl, beat softened ½ cup butter, ½ cup granulated sugar, and remaining ½ cup brown sugar with a hand mixer on medium speed until well combined. Add 2 eggs and blend well.
- Add the dry ingredients to the sugar mixture and beat until well combined. While still mixing, add ½ cup milk, ½ cup of reserved pineapple juice, and 1 teaspoon of almond extract. Carefully pour the cake batter in and spread over the pineapple slices.
- BAKE. Bake for 35–40 minutes until the middle is cooked through and a toothpick inserted in the center comes out clean. Let cool for at least 30 minutes.
- SERVE. Use a sharp paring knife or a rubber spatula and slide it around the inner perimeter of the pan. Place the serving plate (or serving platter), larger than the cake, over the top of the cake and flip. Allow it to sit for another few minutes before carefully removing the pan and let the cake cool.
- Serve this homemade pineapple upside down cake warm or cold with a scoop of Vanilla Ice Cream.
Use Different Pans
- Cast iron skillet. Preheat the skillet in a 325°F oven. Add the pineapple, cherries, and batter, and bake for about 40-45 minutes.
- Bundt pan. Bake at 350°F for 35-40 minutes or until done.
- 9-inch rounds. Bake at 375°F for 30-35 minutes or until done.
Homemade Pineapple Upside Down Cake
Equipment
Video
Ingredients
- 1 cup unsalted butter, divided
- 1½ cups packed light brown sugar, divided
- 1 (20-ounce) can pineapple rings in juice
- 10 maraschino cherries
- 2 cups all-purpose flour
- 2 teaspoons baking powder
- 1 teaspoon salt
- ½ cup granulated sugar
- 2 eggs
- ½ cup milk
- 1 teaspoon almond extract
Instructions
- Preheat the oven to 350°F. Grease a 9×13-inch baking dish.
- Melt ½ cup butter in a medium pot over medium heat. Set remaining ½ cup butter aside to soften.
- Stir 1 cup brown sugar into butter in the pot and bring to a boil, stirring frequently. Continue boiling for 1 minute, then pour into the prepared pan.
- Drain pineapple rings, reserving ½ cup of the juice, and place rings into the bottom of the pan. Place a cherry in the middle of each ring. Set aside.
- In a medium bowl, whisk flour, baking powder, and salt. Set aside.
- In another medium bowl, beat softened ½ cup butter, granulated sugar, and remaining ½ cup brown sugar with a hand mixer until well combined. Add eggs and blend well.
- Add flour mixture to wet mixture and beat until well combined.
- While still mixing, add milk, ½ cup reserved pineapple juice, and almond extract.
- Carefully spread batter over pineapple slices.
- Bake for 35–40 minutes, or until the middle is cooked through and a toothpick inserted in the center comes out clean. Let cool for at least 30 minutes.
- Slide a sharp paring knife or a rubber spatula around the inner perimeter of the pan. Invert a serving platter larger than the cake over the top of the pan. Place one hand on the platter and one hand on the bottom of the pan, then flip. Allow the cake to sit for another few minutes with the pan still covering it, then carefully remove the pan and enjoy!
Notes
- Large cast iron skillet. Preheat the skillet in a 325°F oven. Add the pineapple, cherries, and batter, and bake for about 40-45 minutes.
- Bundt pan. Bake at 350°F for 35-40 minutes or until done.
- Two- 9-inch cake rounds. Bake at 375°F for 30-35 minutes or until done.
Nutrition
Nutrition information is automatically calculated, so should only be used as an approximation.
Recipe FAQ
Make 1-2 days ahead of time and store pineapple cake, covered, on the counter or in the fridge. You can also wrap it with plastic and foil and freeze it for up to 2 months.
Store the cake covered with plastic or in an airtight container at room temperature for up to 2 days, in the refrigerator for about 3 days, or in the freezer for 3 months.
Growing up my mom would make this cake and I would not eat it! I made this recipe for my Father on Father’s Day because it’s his favorite cake, which was my first attempt to make. This cake is so moist and delicious 😋 it has won me over to Pineapple upside down cakes. Thank you for sharing, a better recipe for a historic dessert.
LOL! There are many recipes I didn’t like as a kid, but LOVE them now. I’m glad you gave it another try!
This is by far the best pineapple upsidedown cake recipe! I made this for my dad for his birthday, as pineapple upsidedown cake is his favorite. He and my husband were in absolute awe of how good this cake is. My mother and I, who aren’t huge fans of pineapple upsidedown cake, also enjoyed it alot. My husband said this was the best cake he’s ever had. Where pineapple upsidedown cake typically seems to be a bit too dry, this cake was moist, full of flavor, and the texture was amazing. My husband’s birthday is in a month and he has already said he wants me to make this again and my dad just wants me to keep him in constant supply of it (lol). Thank you for this recipe!
Oh that is wonderful! That honestly makes me so happy to hear. Thank you so much for the review and I’m glad to hear the cake was such a hit!
Hi Kristin. I am almost 88 yrs old, live in an apt in a senior facility & I bake! We play bingo twice a week & I bake something for the players each time. I have used many of your recipes which have been lovingly eaten by residents who were lucky enough to share. I try to make enough for 18 servings from a 15 x 11″ pan. I sometimes i have to adjust ingredient amounts to accommodate number of servings. So far no problems because your recipes are ‘servings’ adjustable.
Thank you for your great recipes!
You’re welcome!! I’m so glad you enjoy the recipes!
In my opinion, this recipe was very simple and the cake came out beautifully, and delicious!
YOU TURNED A GOOD DESSERT INTO A UPSIDE DOWN PINEAPPLE Cake.
NOW I KNOW WHY THEY CALL IT UPSIDE DOWN.
NICE TRY.
DON’T CRY
You should have made a different dessert. This cake is perfect and meant to be a pineapple upside down cake.
Sorry to hear you didn’t enjoy the cake. Thanks for giving it a try!
This cake is absolutely delish. I made in a 8X10 pan and it turned out lovely. Thanks for such a great recipe
You’re welcome! I’m so glad it was a success! Thanks for giving the recipe a try.
Came out dry. Recipe calls for 9×13” pan but it seems a 8×8” would work betterJeanne
What type of flour?
All purpose flour works great!
Excellent recipe
Thank you!! So glad to hear you enjoyed it!
Cake was dry and actually a bit flavorless. There are so many pop-ups that I couldn’t even make this cake without constantly closing ads! Kinda disappointed
Thanks for your feedback and for giving the recipe a try!
If I cut the recipe in half, will it work in a cake pan?
It should work just fine 🙂
thanks! for some reason, your answer didn’t show until I posted the second comment.
Am going to try this … hope all goes well….. thanks for the recipe
So glad you are! I hope you like it! Good luck!
Are you sure the salt measurement is right in the 2020 version of the cake part of this recipe? One whole teaspoon is a lot of salt for 2 cups of flour. My grandson told me he COULDN’T eat it because of the salt. It tasted way too salty For me, too. I was so disappointed because my grandchildren had never had pineapple upside down cake before. It is a shame because the cake looks so good, but cant be eatEn. I can’t give a rating because of that.
Delicious!!! Great recipe! You could use either extract depending on your preference. I used almond and it came out great tasting.
Glad you liked it! Thank you for sharing that!!
This was my first-eVer attempt to make pineapple Upside-down cake, and it was A hit at our social DISTANCING celebrAtion FOr our mom’s 90th biRthdaY. It turned out beautifully APPETIZING. Your clEar directions Made for a fun prep. I made homemade whipping cream to top off the Perfectly moist servings. OuR mom requested this kind if cake, so Thank you for helping make Her birthday special.
That’s so nice of you to say! Thank you so much for letting me know 🙂 Hope she had a great day!
Loving this cake!
I used crushed pineapple instead of slices but followed your recipe otherwise.
Plan to put this it my recipe file and share with others.
Yay!! Thank you so much!!
I FORGOT THE POSSIBLE ELEVATION DIFFERENCE MIGHT CHANGE COOKING TIME SO IF YOU LIVE HIGH UP IN THE MOUNTAINS LIKE I DO YOU MIGHT NEED AN EXTRA 10 OR 15 MINUTES OF BAKE TIME. I THINK MINE TOOK 50 MIN TOTAL.
Love how easy the recipe was to make. My 5 year old helped me and it was easy enough he could follow it without me.
My cakes currently cooling. Hoping it COMES out of the pan ok. It looks absolutely beautiful. Cant wait to cut into it for hubs birthday tomorrow (i know its best warm but its 97°F in the middle of summer and im not about to use the oven during the day.) We can have it cold and be happy i made i stayed up until MIDNIGHT to make it. I loathe baking in a heat WAVE.
I hope it was a hit! Thanks for sharing that! It’s a great reminder to those who are at higher elevation.
One of my favorite cakes!! It is so moist! Love pineapple!
This cake is not only beautiful, but it is so heavenly! The flavor and texture is amazing. Perfect Summer dessert!
Made this tonight, best dessert I’ve ever made!!!
Woohoo!! I am so glad you liked it! Thank you!
Just made THIS for COMPANy for dinner tonight. It looks amazing. Do I just leave it out on the counter until THIS evening?
Sorry, to have not gotten back to you sooner. I sure hope your company loved it. Yes, I would have left it out.
I’m currently about 20 pregnant with our 5th amazing baby! I have been craving a good carmelized upside down pineapple cake and this recipe looks like the ONLY 1 that will end up being like I want it to be. Will update comment as soon as I’m done eating the 1st slice
Its 8 pm NOw. Should be done before long ! Hopefully it ends up as beautifully as yours has.!.
So, what did you think!! I hope you liked it! I know all about those cravings!
Ive always loved This cake baked in a dutch oven while camping. Now i can get a taste of that at home.
Love pineapple upside down cake and this looks insanely delicious!
Pineapple upside down cake is a big favorite here at our house. delish!
We have so many favorites in our family! One would be pineapple upside down cake. My husbands favorite. He would prefer this over chocolate.my favorite part is the brown sugar that becomes carmelized.so easy to make!
I love pineapple Upside down cake!! Can’t wait to make this!
My husband loves pineapples and when it’s in a cake it is even better! Delicious!
This is such a classic, yummy cake! Sometimes, I just want a fruity dessert & this one is delicious!
My daughter loves pineapple! She can eat an entire can in one sitting if I let her; she will love this dessert!
This looks delicious!! Can’t wait to give it a try!!!
Perfectly caramelized!
Pineapple upside down cake is my husbands favorite. I have tried several different recipes and this is by far the best. I substituted vanilla for the almond extract and used 2 9″ deep cake pans vs the 9×13. Thank you for sharing!
Glad to share 🙂 Thank you for saying this!
your ingredients and directions don’t match- Will use a different recipe
The only thing that was different, was the vanilla & almond extract, but I fixed it 🙂
You’re welcome. Gee, so snappy when she is giving you this recipe for free.
I’ve made this a few times with the almond extract but find it overpowered the taste. I’m making it again as a request from my kids for Christmas and am going to try vanilla extract instead. Otherwise a delicious cake! One of our favorites!!
Hi Kristyn, this cake looks wonderful! I have a question, as I am making this tomorrow for my husband’s birthday. In the ingredients, you have vanilla extract, in the directions, you have almond extract. I’m going to use vanilla unless you tell me different. Thanks!
Kristyn, this looks so good I can almost taste it through my computer screen! I’ve always loved pineapple upside down cake, and this one looks like a winner. : D
Thank you, Joan!! You’re too kind!! 😀